


On The Rooftop

by TheShyGirl



Category: Supernatural
Genre: Background Character Death, Blow Jobs, M/M, One Shot, Smoking
Language: English
Status: Completed
Published: 2021-01-26
Updated: 2021-01-26
Packaged: 2021-03-12 00:54:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,673
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29001798
Author URL: https://archiveofourown.org/users/TheShyGirl/pseuds/TheShyGirl
Summary: Dean’s luck isn’t great, but a chance encounter on the rooftop improves his mood. Unfortunately for him, luck still isn’t on his side.*My work is only to be published on AO3. I do not give permission for this to be re-distributed through any app or other website.*
Relationships: Castiel/Dean Winchester
Comments: 9
Kudos: 63





	On The Rooftop

Dean Winchester climbed the steps to his favorite hiding spot at work - the roof. No one else ever came up there. It was his personal haven, something he desperately needed today. He’d been working at Carver Publications for over a year as a personal assistant to the CEO and sole-proprietor, Carver Edlund.

In that time, he’d fulfilled a multitude of duties, but what he really wanted was to be an editor. Mr. Edlund had passed on works to Dean to check over more than once. He’d finally decided that Dean’s skills were being wasted as an assistant and agreed to make him an editor. Dean had received the good news on Friday and was told they’d start the paperwork as soon as they got in on Monday. 

Dean had practically been vibrating with excitement Monday morning. It was at about half-past nine when his phone rang and he’d received the news that Mr. Edlund had an aneurysm that had burst. The man hadn’t known about it and had been feeling perfectly fine. As he was walking out to his car that morning, he’d just hit the ground and was gone before the first person had even reached him. 

Work after that had been like walking through a dream. Dean didn’t even know what he was supposed to do. Was he supposed to take calls, take messages, and tell people someone would be in contact with them? Should he help someone else? Start going through Mr. Edlund’s projects? He definitely considered going through the desk to see if perhaps the paperwork for his promotion was sitting in there. If it wasn’t, he knew his chance of becoming an editor was going to be gone, too.

About halfway through the day, Mr. Edlund’s attorney had shown up to shed some light on the situation. The company was going to be taken over by Mr. Edlund’s only son, Castiel Novak, who would be in the next day. All projects were on hold and anyone calling would have to leave a message for Mr. Novak to return. 

Dean thought that was bullshit and was definitely surprised to learn that Carver had turned the business over to his son. As far he knew, they were estranged. Dean never received any calls from that name and there were no family photos in the office. Any time Carver ever mentioned family, it was always with a hint of sadness. 

Despite not knowing anything for sure, Dean automatically assumed Castiel was a brat. After all, what kind of kid cuts ties with their dad, especially when their dad was such an awesome person? His assumption was only cemented when Tuesday came and went and Castiel never showed up.

It’s what led to Dean being up on the roof at six in the evening. He would normally stay until six or seven. Sometimes it would be later if Carver needed him. For that reason, he planned to stick around until seven, after most people had gone home. He rested his forearms on the ledge and looked out over the nearly empty parking lot. The only people remaining would be the cleaning crew and a few others like himself who were always trying to go the extra mile. 

He desperately wished for a cigarette. Dean didn’t consider himself a smoker, but when he was stressed something about the acrid taste and the plume of smoke from his lips was calming. Stress was eating him up at this point. So many people had been calling to get information from him, info that he didn’t have because Castiel was supposed to be making the decisions. At this point, he didn’t even know if he wanted to continue working at Carver Publications. Working for an ungrateful brat didn’t sound like something he would tolerate well. There was always the chance that Castiel would sell the company, too. Then what would he do? It was all just getting to him. 

The sound of the door opening had him spinning around in time to see a man he didn’t recognize step out. He was dressed in a suit with a blue tie and wore a long tan trench coat over it. His dark hair looked like he’d been running his hands through it and the last glimmers of twilight reflected in his blue eyes. He seemed just as surprised to see Dean as Dean was to see him. 

“Um, hi,” the man said. “Do you care if I smoke out here?”

Dean leaned back against the ledge. “Free world.” He didn’t recognize the guy, but that wasn’t a big surprise. There were more than a few people in the office he’d never officially come face-to-face with. He watched as the man stepped further out onto the roof and pulled a pack of cigarettes from his coat pocket. After tapping the pack on his hand, he pulled one out to place between his lips. As he lit the tip, he noticed Dean watching him. 

“Would you like one?”

“Yeah, actually, if you don’t mind.” He approached the man as a cigarette was held out to him. When the man held up a lighter and flicked it on, Dean leaned forward, holding the cigarette to his lips, and sucked in a breath. In that short moment, as he felt the heat, his eyes slid up and locked with the man’s blue ones. There was something familiar there, but he couldn’t place it. Releasing the breath, he asked, “Have we met?”

The man stepped away and over towards the ledge Dean had just been at. “I doubt it. I’m kind of new here.” He blew a few smoke rings out into the air, watching as they dissipated in front of him. 

Dean hummed an acknowledgment as he returned to his spot. He sunk down to the ground, leaning back against the bricks. “Must be a hell of a time to have started. Boss is dead and now we’re working for his spoiled brat who doesn’t even have the decency to show up.” He took another drag, appreciating how the bitter heat seemed to match his own feelings.

The man wore a tight-lipped smile as he looked down at Dean. “Maybe he wanted to be here, but things like delayed planes and shitty traffic kept him from it.”

Shrugging as best he could, Dean said, “Maybe. He could have called. Or sent an email. I have been fielding calls left and right for two days and I don’t know what to tell anyone.”

“You’re Carver’s assistant?” He sounded surprised. 

“Was. Why is that so shocking?”

Turning his eyes back to the skyline, the man said, “I guess I just assumed his assistant would be a little nerdy guy like he is...was. You look more like one of the models brought in for a book cover.”

Dean laughed, smoke billowing out along with the sound. “Yeah, right.”

Stepping away from the ledge to better see Dean, he said, “It’s true.”

Seeing the soft smile, Dean felt that little twinge in his stomach, like a single butterfly taking flight. “Are you hitting on me?” He kept his tone playful. 

The man’s smile deepened and he looked down at his shoes. “Maybe.” After a deep sigh, he said, “But I suppose that would be inappropriate. Workplace relations and all.”

Not wanting to pass up the opportunity for a secondary release of stress, Dean pushed back to his feet. He snubbed the end of the cigarette against the ledge and dropped it by his feet. “Nothing inappropriate. I don’t know you. You don’t know me. We’re just two guys on a roof.”

Looking back up at Dean, he parroted his words back to him with a grin. “Are you hitting on me?”

Dean stepped closer and lowered his voice. “Is it working?”

“Remarkably well.” They held each other’s gaze until the man turned away and tossed his half-spent cigarette down. “I shouldn’t.” He started to step in the direction of the door, but a hand on his arm pulled him to a stop.

“Look, I’ve had a shitty few days. On Friday, Carver said he was finally going to make me an editor. It was all I’ve ever wanted. We were supposed to start the paperwork yesterday, but… Anyway...I don’t know about you, but I could use a little no-strings fun. I’m about to be working for a shitty little brat of a boss and so are you. So, how about we enjoy what we can now?” Dean moved into the man’s space, close enough that they were nearly touching. “Like each other?”

The flash of desire in the man’s blue eyes was the only warning. Within the next second, Dean found himself pressed hard against the man, strong arms squeezing him close. The mouth moving against his was firm and incessant and he gave in quickly, parting his lips to let their tongues slide together. 

Dean was practically fist-pumping in his mind over this win. This was exactly what he needed and he sent a hopeful prayer that this stranger didn’t back off yet again. Unable to move his arms much, he gripped the edge of the man’s coat with his fingers to keep him close. 

Feeling the light tug, the man loosened his hold and pulled back with a smile. “Afraid I’m gonna run away?” His hands moved to Dean’s shoulder as he pushed gently, walking him backwards until he was against the wall by the door. 

“Didn’t know if you were gonna fall victim to a sense of morality or duty or something,” Dean bantered, sounding a little breathless. 

The man shrugged. “I have a lot to do, but I can catch up tomorrow. For now, I’ll just be a guy on the roof.” He pressed his body to Dean’s, effectively trapping him against the wall, and resumed their kiss. With his hands free, he slid them up and down the white shirt sleeves of Dean’s button-up, feeling the muscles underneath.

Wanting to do the same, Dean quickly became annoyed at the layers of clothes the man was wearing. Without breaking the kiss, he pushed at the material of the coat. He was amazed by the man’s ability to maintain the kiss while shedding both his trench coat and suit jacket, letting them fall to the dirty rooftop without a care. 

Any thoughts beyond that were momentarily lost as the man roughly shoved his leg between Dean’s, providing some friction to his quickly hardening member that was working to tent his black dress pants. Judging from the hardness now pressed against his left thigh, he wasn’t the only one intending to take this further. 

Dean broke away to get some air and his head thumped onto the bricks behind him as the man began a trail of kisses down the side of his neck. “So fucking glad I met you,” Dean mumbled as he let his hands press into the muscles of the man’s arms. Whatever this guy did at the firm, he obviously worked out when he could. When the man’s lips locked onto that spot right below his ear, Dean squirmed against the thigh between his legs. 

“What? Is that a special spot?” a smile colored his words and he paid a little more attention to that spot. 

“Maybe you could quit fucking around and get to fucking me instead,” Dean grunted as he found a particularly pleasurable way to grind down. 

The man pulled away with a laugh. “Fuck you? How? I didn’t think to bring lube and condoms to the roof. Did you?” He looked around jokingly. “Do you have some stashed up here for your rooftop seductions?”

Dean had to concede that the man had a point, frustrating though it was. Maybe he would create a stash on the roof in case he and this guy were to meet up again. “Enough,” he growled in annoyance. He reached between them and began undoing the man’s belt and front of his suit pants. “Let’s do something else.” 

The man bit back a moan as he felt Dean’s hand slid down and wrapped around the hardness in his pants. “Yeah, something else sounds good.”

Smiling at the reaction, Dean said, “You better be ready to return the favor.” Without another word, he pulled the man’s dick from his pants and dropped to his knees. Seeing how gorgeous and large the man was, Dean was even more upset about their lack of getting to fuck. That would have definitely cleared his mind. Getting to the job at hand though, he licked up and down the sides before swallowing around the head. 

The man jolted from the sudden pleasure. One hand held his shirt out of the way while the other went to the back of Dean’s head, steering his ministrations. He couldn’t control his hips as he pumped forward into Dean’s mouth.

While Dean felt confident in his skills, this man’s cock was hitting him at his limit. Thankfully, the hand on the back of his head wasn’t too forceful and he was able to move enough to not have any trouble. This might not be his first time giving head, but Dean had to admit that the way the guy took control brought a new thrill to it.

The man had been without satisfaction, even from himself, for too long. Dean’s mouth was doing wonders. The way it swallowed around him, squeezing in the warmth was almost too much. With Dean being so pretty though, the man knew what he wanted to do. He pushed Dean off him and began jerking his cock over Dean’s face.

“Ooh, kinky,” Dean purred before opening his mouth eagerly, tongue wagging.

The sight would have made anyone come. With a few tight strokes, he began spurting across Dean’s face, cum landing across his nose, his chin, some landing in his mouth. It was a beautiful sight for sure. 

“Mmm…” Dean was happy to play up this guy’s fantasy as he licked around his mouth, collecting as much cum with his tongue as possible. Wanting to make a good impression, he used a finger to scoop up some of the rest that had landed on his face, before licking the finger clean. 

The man smiled, seemingly pleased as he reached down for his suit jacket and pulled out a pocket square. Unfolding the cloth, he proceeded to clean Dean’s face of all the remaining cum. “Sorry. Couldn’t seem to help myself.”

Dean laughed. “Did I look like I minded?”

“You looked fucking amazing.” 

Cocky grin in place, Dean got back to his feet. “Yeah? I get some appreciation, right?” Dean was already in the process of undoing his pants.

Tossing the soiled square back to his jacket, the man quickly took over for Dean. With the fastenings undone, he gripped the sides of the dress pants and pulled them down, sinking to his knees as he went. There was a pair of gray boxer-briefs underneath with a very obvious outline. A darker gray spot at the tip made him grin. “Wet already, huh?” he joked. 

“Your mouth do anything useful or do you just talk?” Dean shot back. 

The man made a scoffing noise. “Aren’t you a demanding little shit. I’ll be sure to remember that.” He wasted no more time and pulled Dean’s underwear down to join his pants, freeing a cock that nearly made his mouth water. It was thicker than it had seemed behind the fabric with noticeable veins. “Why the fuck are you working here? With a dick like this, you should be in porn.” He didn’t really care about the answer as he wrapped a hand around the shaft and angled it for his mouth. 

Dean smirked at the porn comment, but as he watched the dark-haired man’s lips stretch around him, any significant thought quickly left him. This was definitely the kind of stress-relief he needed. He let his head tilt back as he felt his dick getting enveloped in the tight warmth of the man’s mouth. It felt so good and to his amazement, it didn’t stop. The man was sliding further and further down his shaft. He had to see it. Jerking his head back forward, he looked down and watched as the man began to bob his head. Every few slides forward, the man would surge forward and Dean could feel his cock getting squeezed as it pushed into the man’s throat. 

The man pulled back, saliva dripping down his chin as he took a moment to catch his breath. “Fuck,” he said as he panted. “You taste amazing.” Focusing back on his task, he took Dean back into his mouth. He pressed forward as far as he could until his nose was nearly touching Dean’s body, but he couldn’t quite get there.

“Holy shit!” Dean was watching with fascination and trying not to come immediately. “Dude, I’m not gonna last if you keep doing that. Your throat is like a vice!”

Backing off Dean again, the man coughed before saying, “Getting you off is the point.” His voice was gritty from the workout he’d been putting his throat through. Despite what he said, he did stop going so deep, though it may have been as much for his own benefit as Dean’s. He sped up and added a hand to help with what he was no longer swallowing down. 

“Yes! Like that!” Dean let his head fall back once more and rested a hand on the thick head of hair below him. He could feel himself getting close and at a much better pace. The man was sucking him just the way he liked and short of being fucked, Dean couldn’t think of anything better. Slowly his hips began to sway into the motion and soft moans started falling from his lips. 

Realizing how close Dean was, the man reached around and probed a finger between two taut cheeks, quickly finding the spot he was searching for. Without any lube, he didn’t dare press in, but just pressing lightly against the rim was good enough, judging by the sound it elicited. 

Feeling that thick finger at his hole caused a noise Dean was sure he’d never made before. It was the strangest, most desperate sounding cry he’d ever heard. More than anything he wanted to feel that finger inside him, but had to be content with the thought of next time. He damn sure wanted there to be a next time. The extra sensations ended up being more than Dean could take. He had no intention of pulling out as the guy had though. Right as he felt that so familiar tightening, he brought both hands to the back of the man’s head, holding him in place as he surged forward, pressing deep inside. With poorly muffled grunts, he let pulse after pulse pour down the man’s throat. It felt like every ounce of stress and tension he’d been holding was sliding right out of his body. Feeling a hand press against his leg, Dean immediately let go of the man’s head so he could pull back and breathe.

The man had definitely not been expecting that, but at least his skills allowed for what Dean did. He filled his lungs and immediately began coughing, cum and spit sputtering from his mouth. Once his coughing subsided, he was still panting for breath as he looked up at Dean with a smile. “Good?”

Everything in the world was good to Dean at the moment. Nothing else mattered. Looking down at that face with cum and spit dribbling down his chin, dripping onto his fancy white shirt, Dean was blown away by how fucking beautiful the guy looked. “Shit. You said I should be in a porn, but look at you.”

The man laughed as he got back to his face. “Well, that soun-” He didn’t get to finish the sentence as Dean pressed him back against the wall for a searing kiss. Their tastes flowed together as their tongues winded around, each caressing the other. The man didn’t doubt that there was a definite promise in this kiss.

Calming down, Dean slowly pulled back from the kiss and stepped away, giving the man some breathing room. “Sorry. Couldn’t seem to help myself.”

The man smiled at hearing his own words back. “Did I look like I minded?” 

Both had to laugh and then got to work righting their clothes. 

As he picked up his rather disgusting pocket square, suit jacket, and coat, the man had a question he had to ask. “Hey. You twice called Carver’s son a brat. Can I ask why?”

Dean shrugged. “Never got any calls from him. He never came by the office. Carver always seemed to act like they were estranged. I guess I don’t really know. But he didn’t have the respect to fucking show up today, so that says a lot. Plus, there’s no way he’s going to believe me about being promoted to editor when I’m a fuckin’ assistant.”

The man seemed to frown. “I suppose some of that is true.” With his suit jacket and trench coat thrown over his arm, he looked up at Dean. “What’s your name?”

Smiling, he said, “Dean. You want my number, too? I wouldn’t mind doing this again.”

Turning away with a grin of his own, the man asked, “What about last name?”

“Winchester.”

“Dean Winchester,” he intoned. He walked over to the door to the stairs before looking back at Dean. “I promise you, Dean Winchester. First thing tomorrow, you will be an editor.”

“Oh. Is that so?” Dean laughed as he gathered up his wallet and phone from where they’d slid out of his pockets. “How do you think you’ll manage that?”

“Because I’m the brat, but you can call me Castiel. I’ll see you in the morning, Dean.” Shooting a wink at his now slack-jawed assistant, Castiel pulled open the door and went inside. 

The door closed and still Dean stood there, incapable of moving. “Fuck.” 


End file.
